3-[1-(3-Haloalkyl)triazolyl]phenyl sulphide derivatives as acaricides and insecticides

ABSTRACT

The present invention constitutes new 3-[1-(3-haloalkyl)triazolyl]phenyl sulphide derivatives of the formula (I) 
     
       
         
         
             
             
         
       
     
     in which A 1 , A 2 , B 0 , B 1 , B 2 , B 3 , R 1 , R 2  and n are as defined in the description, to their use as acaricides and insecticides for controlling animal pests, and to processes for preparing them.

FIELD OF THE INVENTION

The present invention relates to new 3-[1-(3-haloalkyl)triazolyl]phenylsulphide derivatives, to their use as acaricides and insecticides forcontrolling animal pests, and to processes for preparing them.

BACKGROUND OF THE INVENTION

Various substituted phenylheterocyclyl sulphide derivatives and theirinsecticidal and acaricidal activity have already been described in theliterature, in WO 1999/055668, WO 2006/043635 and JP 2007-284356.

The active compounds already known from the specifications identifiedabove exhibit disadvantages in their use, possessing either zero orinadequate insecticidal and/or acaricidal activity toward animal pests,not least at relatively low application rates.

It is an object of the present invention, therefore, to provide3-[1-(3-haloalkyl)triazolyl]phenyl sulphide derivatives which can beused as insecticides and/or acaricides with a satisfactory or improvedinsecticidal and/or acaricidal activity towards animal pests,particularly at relatively low application rates, with a highselectivity and high compatibility in crop-plant cultures.

SUMMARY OF THE INVENTION

New compounds have now been found of the formula (I)

in whichA¹ is CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂, CF₂Cl, CFCl₂ or (C₂-C₆)haloalkyl,A² is hydrogen,B⁰ is hydrogen, amino, halogen, cyano, nitro, alkyl, haloalkyl,alkylthio, haloalkylthio, alkoxy or haloalkoxy,B¹, B² and B³ independently of one another are each hydrogen, halogen,cyano, nitro, alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl,alkoxycarbonylalkyl, alkoxyalkyl, alkenyl, haloalkenyl, cyanoalkenyl,alkynyl, haloalkynyl, cyanoalkynyl, alkoxy, haloalkoxy, cyanoalkoxy,alkoxycarbonylalkoxy, alkoxyalkoxy, alkylthio, haloalkylthio,alkoxyalkylthio, alkylsulphinyl, haloalkylsuiphinyl,alkoxyalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,alkoxyalkylsulphonyl, acyl, haloalkylcarbonyl, carboxyl, alkoxycarbonylor NR³R⁴, where R³ and R⁴ independently of one another are hydrogen,alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl,alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl,acyl or alkoxycarbonyl, or R³ and R⁴, together with the N atom to whichthey are attached, may form an optionally substituted saturated orunsaturated, five- to eight-membered ring which is optionallyinterrupted by heteroatoms,n is the number 0, 1 or 2,R¹ is hydrogen or alkyl,R² is hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cyanoalkyl,alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl orhaloalkoxyalkyl, or is optionally substituted cycloalkyl or cycloalkenyleach of which is optionally interrupted by one or more heteroatoms.

The compounds of the formula (I) may possibly exist in differentpolymorphic forms or as a mixture of different polymorphic forms. Notonly the pure polymorphs but also the polymorph mixtures are subjectmatter of the invention and can be used in accordance with theinvention.

The compounds of the formula (I) may comprise diastereomers orenantiomers.

The compounds of the invention are defined in general terms by theformula (I). Preferred substituents and ranges of the radicals given inthe formulae referred to above and below are defined

whereA¹ preferably is CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂, CF₂Cl, CFCl₂ or(C₂-C₆)haloalkyl,A² preferably is hydrogen,B⁰ preferably is hydrogen, amino, halogen, cyano, nitro, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxyor (C₁-C₆)haloalkoxy,B¹, B² and B³ independently of one another preferably are each hydrogen,halogen, cyano, nitro, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,(C₂-C₇)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl (C₂-C₆)cyanoalkenyl, (C_(r)C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₂-C₅)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₃)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₃)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylsulphinyl, (C₁-C₆)haloalkylsulphinyl,(C₁-C₃)alkoxy-(C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)haloalkylsulphonyl, (C₁-C₃)alkoxy-(C₁-C₆)alkylsulphonyl,(C₁-C₇)acyl, (C₂-C₅)haloalkylcarbonyl, carboxyl, (C₂-C₇)alkoxycarbonylor NR³R⁴, where R³ and R⁴ independently of one another are hydrogen,(C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₇)acyl,(C₂-C₇)alkoxycarbonyl, or R³ and R⁴, together with the N atom to whichthey are attached, may form an optionally (C₁-C₄)alkyl-, (C₁-C₄)alkoxy-,(C₁-C₄)haloalkyl-substituted saturated or unsaturated, five- orsix-membered ring which is optionally interrupted by heteroatoms,n preferably is the number 0, 1 or 2,R¹ preferably is hydrogen or (C₁-C₄)alkyl,R² preferably is hydrogen, halogen, cyano, nitro, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl or(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, or is optionally substituted(C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkenyl each of which is optionallyinterrupted by one or more heteroatoms.

DETAILED DESCRIPTION OF THE INVENTION

The compounds of the invention are defined in general terms by theformula (I). Very preferred substituents and ranges of the radicalsgiven in the formulae referred to above and below are defined

whereA¹ very preferably is CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂, CF₂Cl, CFCl₂ or(C₂-C₆)haloalkyl,A² very preferably is hydrogen,B⁰ very preferably is hydrogen, amino, halogen, cyano, nitro,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,(C₁-C₄)alkoxy or (C₁-C₄)haloalkoxy,B¹, B² and B³ independently of one another very preferably are eachhydrogen, halogen, cyano, nitro, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkenyl, (C₁-C₄)alkoxy or (C₁-C₄)haloalkoxy,n very preferably is the number 0 or 1,R¹ very preferably is hydrogen or (C₁-C₂)alkyl,R² very preferably is hydrogen, halogen, cyano, nitro, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,(C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, C₄)alkoxy-(C₁-C₄)alkyl or(C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, or is optionally substituted(C₃-C₆)cycloalkyl or (C₃-C₆)cycloalkenyl each of which is optionallyinterrupted by one or more heteroatoms.

The compounds of the invention are defined in general terms by theformula (I). Especially preferred substituents and ranges of theradicals indicated in the formulae referred to above and below aredefined

whereA¹ especially preferably is CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂, CF₂Cl,CFCl₂, CF₂CF₃, CF₂CHF₂ or CF₂CF₂Cl,A² especially preferably is hydrogen,B⁰ especially preferably is hydrogen, methyl, ethyl, fluoro, chloro,methoxy, cyano, CHF₂, CF₃ or OCF₃,B¹ especially preferably is hydrogen,B² especially preferably is hydrogen, methyl, ethyl, fluoro, chloro,methoxy, cyano, CHF₂, CF₃ or OCF₃,B³ especially preferably is hydrogen,n especially preferably is the number 0 or 1,R¹ especially preferably is hydrogen,R² especially preferably is hydrogen, CF₃, cyano, methyl, ethyl, propyl,isopropyl, cyclopropyl, CHF₂, CF₂Cl, CCl₃, CFCl₂, CF₂CF₃, CF₂CHF₂,CH₂CF₃, CH₂CHF₂ or CF₂CF₂Cl.

The definitions of radicals, and explanations, that are given above ingeneral or in ranges of preference may be combined arbitrarily with oneanother, thus including combinations between the respective ranges andranges of preference. The definitions and explanations apply to the endproducts and also to the precursors and intermediates accordingly.

Preferred in accordance with the invention are the compounds of theformula (I) in which there is a combination of the definitions givenabove as being preferred (preferably).

Very preferred in accordance with the invention are the compounds of theformula (I) in which there is a combination of the definitions givenabove as being very preferable.

Especially preferred in accordance with the invention are the compoundsof the formula (I) in which there is a combination of the definitionsgiven above as being especially preferable.

Saturated or unsaturated hydrocarbon radicals such as alkyl, alkanediylor alkenyl may in each case, both alone and in conjunction withheteroatoms, as in alkoxy, for example, be—where possible—eitherstraight-chain or branched.

Any substituted radicals may, unless indicated otherwise, be substitutedone or more times, and the substituents in the case of multiplesubstitutions may be alike or different.

In the definitions of radicals that are stated as being preferred,halogen (halo) is fluoro, chloro, bromo and iodo, very preferablyfluoro, chloro and bromo, and especially preferably fluoro and chloro.

The following compounds of the formula (I-A) are included specifically.

TABLE 1 (I-A)

A¹ B⁰ B² R² n CHF₂ Me Me CF₃ 0 CHF₂ Me Me CHF₂ 0 CHF₂ Me Me CF₂CF₃ 0CHF₂ Me Me CF₂CHF₂ 0 CHF₂ Me Me CF₂CF₂Cl 0 CHF₂ Me Me CN 0 CHF₂ Me Me Me0 CHF₂ Me Me Pr-i 0 CHF₂ Me Me Pr-c 0 CHF₂ Me Me H 0 CHF₂ Me Me CH₂CF₃ 0CHF₂ Me Me CH₂CHF₂ 0 CHF₂ Me Me CF₃ 1 CHF₂ Me Me CHF₂ 1 CHF₂ Me MeCF₂CF₃ 1 CHF₂ Me Me CF₂CHF₂ 1 CHF₂ Me Me CF₂CF₂Cl 1 CHF₂ Me Me CN 1 CHF₂Me Me Me 1 CHF₂ Me Me Pr-i 1 CHF₂ Me Me Pr-c 1 CHF₂ Me Me H 1 CHF₂ Me MeCH₂CF₃ 1 CHF₂ Me Me CH₂CHF₂ 1 CF₂CF₃ Me Me CF₃ 0 CF₂CF₃ Me Me CHF₂ 0CF₂CF₃ Me Me CF₂CF₃ 0 CF₂CF₃ Me Me CF₂CHF₂ 0 CF₂CF₃ Me Me CF₂CF₂Cl 0CF₂CF₃ Me Me CN 0 CF₂CF₃ Me Me Me 0 CF₂CF₃ Me Me Pr-i 0 CF₂CF₃ Me MePr-c 0 CF₂CF₃ Me Me H 0 CF₂CF₃ Me Me CH₂CF₃ 0 CF₂CF₃ Me Me CH₂CHF₂ 0CF₂CF₃ Me Me CF₃ 1 CF₂CF₃ Me Me CHF₂ 1 CF₂CF₃ Me Me CF₂CF₃ 1 CF₂CF₃ MeMe CF₂CHF₂ 1 CF₂CF₃ Me Me CF₂CF₂Cl 1 CF₂CF₃ Me Me CN 1 CF₂CF₃ Me Me Me 1CF₂CF₃ Me Me Pr-i 1 CF₂CF₃ Me Me Pr-c 1 CF₂CF₃ Me Me H 1 CF₂CF₃ Me MeCH₂CF₃ 1 CF₂CF₃ Me Me CH₂CHF₂ 1 CF₂CF₂Cl Me Me CF₃ 0 CF₂CF₂Cl Me Me CHF₂0 CF₂CF₂Cl Me Me CF₂CF₃ 0 CF₂CF₂Cl Me Me CF₂CHF₂ 0 CF₂CF₂Cl Me MeCF₂CF₂Cl 0 CF₂CF₂Cl Me Me CN 0 CF₂CF₂Cl Me Me Me 0 CF₂CF₂Cl Me Me Pr-i 0CF₂CF₂Cl Me Me Pr-c 0 CF₂CF₂Cl Me Me H 0 CF₂CF₂Cl Me Me CH₂CF₃ 0CF₂CF₂Cl Me Me CH₂CHF₂ 0 CF₂CF₂Cl Me Me CF₃ 1 CF₂CF₂Cl Me Me CHF₂ 1CF₂CF₂Cl Me Me CF₂CF₃ 1 CF₂CF₂Cl Me Me CF₂CHF₂ 1 CF₂CF₂Cl Me Me CF₂CF₂Cl1 CF₂CF₂Cl Me Me CN 1 CF₂CF₂Cl Me Me Me 1 CF₂CF₂Cl Me Me Pr-i 1 CF₂CF₂ClMe Me Pr-c 1 CF₂CF₂Cl Me Me H 1 CF₂CF₂Cl Me Me CH₂CF₃ 1 CF₂CF₂Cl Me MeCH₂CHF₂ 1

TABLE 2 A¹, R² and n as indicated in Table 1 B⁰ = H; B² = CN

TABLE 3 A¹, R² and n as indicated in Table 1 B⁰ = H; B² = Me

TABLE 4 A¹, R² and n as indicated in Table 1 B⁰ = H; B² = CHF₂

TABLE 5 A¹, R² and n as indicated in Table 1 B⁰ = F; B² = CN

TABLE 6 A¹, R² and n as indicated in Table 1 B⁰ = F; B² = Me

TABLE 7 A¹, R² and n as indicated in Table 1 B⁰ = F; B² = CHF₂

TABLE 8 A¹, R² and n as indicated in Table 1 B⁰ = Cl; B² = CN

TABLE 9 A¹, R² and n as indicated in Table 1 B⁰ = Cl; B² = Me

TABLE 10 A¹, R² and n as indicated in Table 1 B⁰ = Cl; B² = CHF₂

TABLE 11 A¹, R² and n as indicated in Table 1 B⁰ = Me; B² = Cl

TABLE 12 A¹, R² and n as indicated in Table 1 B⁰ = F; B² = Cl

TABLE 13 A¹, R² and n as indicated in Table 1 B⁰ = H; B² = Cl

TABLE 14 A¹, R² and n as indicated in Table 1 B⁰ = H; B² = CF₃

Preparation Processes

The compounds of the general formula (I) can be prepared using themethods described in application WO 1999/055668. Alternatively to thesedescribed methods, the compounds of the formula (I) may also be preparedby processes (A) or (A′).

where A¹, B⁰, B¹, B², B³, R¹ and R² are as defined above and A^(1a) isalkyl, preferably (C₁-C₆)alkyl.

Anilines of the formula (VII) are either available commercially or canbe prepared by known methods. The anilines (VII) are converted withsodium nitrite in the presence of hydrochloric acid into thecorresponding diazonium salt and then reduced with tin chloride to givehydrazines of the formula (VI). In the presence of esters (VIII), thehydrazines (VI) are converted into the corresponding hydrazides (V).Hydrazides (V) are reacted with formamidine hydrochloride in thepresence of a base, such as sodium hydrogen carbonate, the triazoles ofthe formula (IV-A) being formed. Alternatively the hydrazines (VI) canbe converted into the corresponding amidrazones of the formula (X) inthe presence of amidines of the formula (XI) or salts thereof such as,for example, amidinium hydrochlorides or amidinium sulphates.Amidrazones of the formula (X) are reacted with an orthoformate such as,for example, methyl orthoformate or ethyl orthoformate, forming thetriazoles of the formula (IV-A). The triazoles of the formula (IV-A) mayalso be prepared via copper-catalyzed coupling reaction with the boronicacids of the formula (VIII), and triazoles of the formula (IX-A) (cf. WO1997055668). The sulphochlorination of the triazoles (IV-A) withchlorosulphonic acid yields the corresponding sulphonyl chlorides(III-A). The sulphonyl chlorides (III-A) can be reduced to give thedisulphides (II-A) by methods known from the literature, such as iron inhydrochloric acid, hydrogen iodide or iodides, for example. The reactionof the disulphides with electrophiles of the formula (IX), where AG is aleaving group such as chloro, bromo, tosylate, mesylate or triflate,yields the sulphides (I-Aa). The thioethers are converted into thecorresponding sulphoxides (I-Ab) and sulphones (I-Ac) by reaction withoxidizing agents such as, for example, meta-chloroperbenzoic acid.

The following intermediates are new and also subject matter of theinvention.

Compounds of the formula (II-A):

where A¹, B⁰ and B² are as defined above and B¹ and B³ are hydrogen.

Compounds of the formula (III-A)

where A¹, B⁰ and B² are as defined above and B¹ and B³ are hydrogen.

Compounds of the formula (IV-A)

whereB¹ and B³ are hydrogen,

if A¹ is CHF₂, CF₂CHF₂ or CF₂CF₂Cl,

B⁰ is hydrogen, methyl, ethyl, fluoro, chloro, methoxy, cyano, CHF₂, CF₃or OCF₃,B² is hydrogen, methyl, ethyl, fluoro, chloro, methoxy, cyano, CHF₂, CF₃or OCF₃, if A′ is CF₂CF₃,B⁰ is hydrogen, methyl, ethyl, fluoro, methoxy, cyano, CHF₂, CF₃ orOCF₃,B² is methyl, ethyl, fluoro, chloro, methoxy, cyano, CHF₂, CF₃ or OCF₃.

Compounds of the formula (V)

whereB¹ and B³ are hydrogen,

A¹ is CHF₂, CF₂CF₃, CF₂CHF₂ or CF₂CF₂Cl,

B⁰ is methyl, ethyl, fluoro, chloro, methoxy, cyano, CHF₂, CF₃ or OCF₃,B² is hydrogen, methyl, methoxy, ethyl, fluoro, chloro, cyano, CHF₂, CF₃or OCF₃,and B² is not methyl if A¹ is CHF₂,and B² is not methoxy if A¹ is CF₂CF₃.

Compounds of the formula (X)

A¹ is CH₂F, CF₂CF₃, CF₂CHF₂ or CF₂CF₂Cl,

B⁰ is hydrogen, methyl, ethyl, fluoro, chloro, methoxy, cyano, CHF₂, CF₃or OCF₃,B² is hydrogen, methyl, ethyl, fluoro, chloro, methoxy, cyano, CHF₂, CF₃or OCF₃, and B² is not hydrogen if A¹ is CF₂CF₃.

The active compounds according to the invention, in combination withgood plant tolerance and favourable toxicity to warm-blooded animals andbeing tolerated well by the environment, are suitable for protectingplants and plant organs, for increasing the harvest yields, forimproving the quality of the harvested material and for controllinganimal pests, in particular insects, arachnids, helminths, nematodes andmolluscs, which are encountered in agriculture, in horticulture, inanimal husbandry, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector. They may be preferably employed as plant protection agents. Theyare active against normally sensitive and resistant species and againstall or some stages of development. The abovementioned pests include:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectesspp.

From the class of the Arachnida, for example, Acarus spp., Aceriasheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychusviennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobiapraetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp.,Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Halotydeusdestructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectusmactans, Metatetranychus spp., Nuphersa spp., Oligonychus spp.,Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Geophilus spp., Scutigeraspp.

From the order of the Coleoptera, for example, Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp.,Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.,Anthonomus spp., Anthrenus spp., Apion spp., Apogonia spp., Atomariaspp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Cassida spp.,Cerotoma trifurcata, Ceuthorhynchus spp., Chaetocnema spp., Cleonusmendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica,Ctenicera spp., Curculio spp., Cryptorhynchus lapathi, Cylindrocopturusspp., Dermestes spp., Diabrotica spp., Dichocrocis spp., Diloboderusspp., Epilachna spp., Epitrix spp., Faustinus spp., Gibbium psylloides,Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorphaelegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp.,Lachnosterna consanguinea, Lema spp., Leptinotarsa decemlineata,Leucoptera spp., Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp.,Lyctus spp., Megascelis spp., Melanotus spp., Meligethes aeneus,Melolontha spp., Migdolus spp., Monochamus spp., Naupactusxanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilussurinamensis, Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetoniajucunda, Phaedon cochleariae, Phyllophaga spp., Phyllotreta spp.,Popillia japonica, Premnotrypes spp., Psylliodes spp., Ptinus spp.,Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorusspp., Stemechus spp., Symphyletes spp., Tanymecus spp., Tenebriomolitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechusspp., Zabrus spp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Agromyza spp.,Anastrepha spp., Anopheles spp., Asphondylia spp., Bactrocera spp.,Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata,Chironomus spp., Chrysomyia spp., Cochliomyia spp., Contarinia spp.,Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae,Dasyneura spp., Delia spp., Deiniatobia hominis, Drosophila spp.,Echinocnemus spp., Fannia spp., Gastrophilus spp., Hydrellia spp.,Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Luciliaspp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyiaspp., Phorbia spp., Prodiplosis spp., Psila rosae, Rhagoletis spp.,Stomoxys spp., Tabanus spp., Tannia spp., Tetanops spp., Tipula spp.

From the class of the Gastropoda, for example, Arion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp.,Oncomelania spp., Pomacea spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.,Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp.,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereriabancrofti.

It is furthermore possible to control protozoa, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Collaria spp., Creontiades dilutus, Dasynuspiperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp.,Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus,Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropesexcavatus, Miridae, Monalonion atratum, Nezara spp., Oebalus spp.,Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus,Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoriscastanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.

From the order of the Homoptera, for example, Acyrthosipon spp.,Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp.,Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphiscardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridiaapicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthumsolani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp.,Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida,Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphonfragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphisjuglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli,Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp.,Diaphorina spp., Diaspis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelisbilobatus, Ferrisia spp., Geococcus coffeae, Hieroglyphus spp.,Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp.,Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva spp.,Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monelliacostalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri,Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Ortheziapraelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp.,Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzuspasserinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae,Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona,Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp.,Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphumspp., Saissetia spp., Scaphoides titanus, Schizaphis graminum,Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodesspp., Stictocephala festina, Tenalaphara malayensis, Tinocalliscaryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes spp., Triozaspp., Typhlocyba spp., Unaspis spp., Viteus vitifolii Zygina spp.

From the order of the Hymenoptera, for example, Athalia spp., Diprionspp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus, Porcellio scaber.

From the order of the Isoptera, for example, Acromyrmex spp., Atta spp.,Cornitermes cumulans, Microtermes obesi, Odontotermes spp.,Reticulitermes spp.

From the order of the Lepidoptera, for example, Acronicta major,Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyeloistransitella, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathrabrassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius,Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana,Carpocapsa pomonella, Carposina niponensis, Chematobia brumata, Chilospp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp.,Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp.,Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis,Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldanasaccharina, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana,Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Euxoaspp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholithaspp., Hedylepta spp., Helicoverpa spp., Heliothis spp., Hofmannophilapseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella,Kakivoria flavofasciata, Laphygma spp., Laspeyresia molesta, Leucinodesorbonalis, Leucoptera spp., Lithocolletis spp., Lithophane antennata,Lobesia spp., Loxagrotis albicosta, Lymantria spp., Lyonetia spp.,Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Mocis spp.,Mythimna separata, Nymphula spp., Oiketicus spp., Oria spp., Orthagaspp., Ostrinia spp., Oulema oryzae, Panolis flammea, Parnara spp.,Pectinophora spp., Perileucoptera spp., Phthorimaea spp., Phyllocnistiscitrella, Phyllonorycter spp., Pieris spp., Platynota stultana, Plusiaspp., Plutella xylostella, Prays spp., Prodenia spp., Protoparce spp.,Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis,Rachiplusia nu, Schoenobius spp., Scirpophaga spp., Scotia segetum,Sesamia spp., Sparganothis spp., Spodoptera spp., Stathmopoda spp.,Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia spp., Tuta absoluta, Virachola spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Dichroplus spp., Gryllotalpa spp.,Leucophaea maderae, Locusta spp., Melanoplus spp., Periplanetaamericana, Schistocerca gregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp.,Xenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella spp.

From the order of the Thysanoptera, for example, Anaphothrips obscurus,Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens,Frankliniella spp., Heliothrips spp., Hercinothrips femoralis,Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni,Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Aphelenchoides spp.,Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp.,Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.

If appropriate, the compounds according to the invention can, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, or asmicrobicides, for example as fungicides, antimycotics, bactericides,viricides (including agents against viroids) or as agents against MLO(mycoplasma-like organisms) and RLO (rickettsia-like organisms). Ifappropriate, they can also be employed as intermediates or precursorsfor the synthesis of other active compounds.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, water- and oil-basedsuspensions, powders, dusts, pastes, soluble powders, soluble granules,granules for broadcasting, suspension-emulsion concentrates, naturalmaterials impregnated with active compound, synthetic materialsimpregnated with active compound, fertilizers and microencapsulations inpolymeric substances.

The present invention accordingly further provides formulations, andapplication forms prepared from them, as crop protection agents and/orpesticidal agents, such as drench, drip and spray liquors, comprising atleast one of the active compounds of the invention. The applicationforms may comprise further crop protection agents and/or pesticidalagents, and/or activity-enhancing adjuvants such as penetrants, examplesbeing vegetable oils such as, for example, rapeseed oil, sunflower oil,mineral oils such as, for example, liquid paraffins, alkyl esters ofvegetable fatty acids, such as rapeseed oil or soybean oil methylesters, or alkanol alkoxylates, and/or spreaders such as, for example,alkylsiloxanes and/or salts, examples being organic or inorganicammonium or phosphonium salts, examples being ammonium sulphate ordiammonium hydrogen phosphate, and/or retention promoters such asdioctyl sulphosuccinate or hydroxypropylguar polymers and/or humectantssuch as glycerol and/or fertilizers such as ammonium, potassium orphosphorous fertilizers, for example.

Examples of typical formulations include water-soluble liquids (SL),emulsifiable concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and other possible types offormulation are described, for example, by Crop Life International andin Pesticide Specifications, Manual on development and use of FAO andWHO specifications for pesticides, FAO Plant Production and ProtectionPapers—173, prepared by the FAO/WHO Joint Meeting on PesticideSpecifications, 2004, ISBN: 9251048576. The formulations may compriseactive agrochemical compounds other than one or more active compounds ofthe invention.

The formulations or application forms in question preferably compriseauxiliaries, such as extenders, solvents, spontaneity promoters,carriers, emulsifiers, dispersants, frost protectants, biocides,thickeners and/or other auxiliaries, such as adjuvants, for example. Anadjuvant in this context is a component which enhances the biologicaleffect of the formulation, without the component itself having abiological effect. Examples of adjuvants are agents which promote theretention, spreading, attachment to the leaf surface, or penetration.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers. The formulations areprepared either in suitable plants or else before or during theapplication.

Suitable for use as auxiliaries are substances which are suitable forimparting to the composition itself and/or to preparations derivedtherefrom (for example spray liquors, seed dressings) particularproperties such as certain technical properties and/or also particularbiological properties. Typical suitable auxiliaries are: extenders,solvents and carriers.

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethyl sulphoxide, and also water.

All suitable carriers may in principle be used. Suitable solid carriersare:

for example, ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates; suitable solid carriers for granules are: forexample, crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, and also synthetic granules of inorganicand organic meals, and granules of organic material such as paper,sawdust, coconut shells, maize cobs and tobacco stalks; suitableemulsifiers and/or foam-formers are: for example, nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates and also proteinhydrolysates; suitable dispersants are nonionic and/or ionic substances,for example from the classes of the alcohol-POE and/or POP ethers, acidand/or POP-POE esters, alkylaryl and/or POP-POE ethers, fat- and/orPOP-POE adducts, POE- and/or POP-polyol derivatives, POE- and/orPOP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl- orarylsulphonates and alkyl or aryl phosphates or the correspondingPO-ether adducts. Furthermore, suitable oligo- or polymers, for examplethose derived from vinylic monomers, from acrylic acid, from EO and/orPO alone or in combination with, for example, (poly)alcohols or(poly)amines. It is also possible to employ lignin and its sulphonicacid derivatives, unmodified and modified celluloses, aromatic and/oraliphatic sulphonic acids and their adducts with formaldehyde.

Tackifiers such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Other possible additives are perfumes, mineral or vegetable, optionallymodified oils, waxes and nutrients (including trace nutrients), such assalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Stabilizers, such as low-temperature stabilizers, preservatives,antioxidants, light stabilizers or other agents which improve chemicaland/or physical stability may also be present.

There may possibly be further auxiliaries present in the formulationsand the application forms derived from them. Examples of such additivesinclude protective colloids, binders, adhesives, thickeners, thixotropicsubstances, penetrants, retention promoters, stabilizers, sequestrants,complexing agents, humectants and spreaders. Generally speaking, theactive compounds may be combined with any solid or liquid additivecommonly used for formulation purposes.

Suitable retention promoters include all those substances which reducethe dynamic surface tension, such as dioctyl sulphosuccinate, orincrease the viscoelasticity, such as hydroxypropylguar polymers, forexample.

Suitable penetrants in the present context include all those substanceswhich are typically used in order to enhance the penetration of activeagrochemical compounds into plants. Penetrants in this context aredefined in that, from the (generally aqueous) application liquor and/orfrom the spray coating, they are able to penetrate the cuticle of theplant and thereby increase the mobility of the active compounds in thecuticle. This property can be determined using the method described inthe literature (Baur et al., 1997, Pesticide Science 51, 131-152).Examples include alcohol alkoxylates such as coconut fatty ethoxylate(10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseedor soybean oil methyl esters, fatty amine alkoxylates such astallowamine ethoxylate (15), or ammonium and/or phosphonium salts suchas ammonium sulphate or diammonium hydrogen phosphate, for example.

The formulations generally comprise between 0.01 and 98% by weight ofactive compound, preferably between 0.5 and 90%.

The active compounds according to the invention may be used as they areor in their formulations, including a mixture with one or more suitablefungicides, bactericides, acaricides, nematicides, insecticides,microbiologicals, fertilizers, attractants, phytotonics, sterilants,synergists, safeners, semiochemicals and/or plant growth regulators, inorder thereby, for example, to broaden the activity spectrum, to prolongthe duration of action, to increase the rate of action, to preventrepulsion or to prevent development of resistance. Furthermore,combinations of this kind may improve plant growth, raise tolerancetowards abiotic factors such as high or low temperatures, againstdrought or against increased levels of water and/or soil salt. It isalso possible to improve the flowering and fruiting behaviour, thecapacity for germination and rooting, to facilitate harvesting andincrease yields, to influence ripening, to increase the quality and/ornutritional value of the harvested products, to prolong storage lifeand/or to improve the manageability of the harvested products. Generallyspeaking, combining the active compounds of the invention andco-components produces synergistic effects—that is, the activity of themixture in question is greater than the activity of the individualcomponents. In general it is possible to use the combinations not onlyin premixes, tankmixes or ready-made mixes but also in seedapplications.

Particularly favourable co-components are, for example, those listedbelow.

Insecticides/Acaricides/Nematicides

The active compounds identified here by their common name are known andare described in the pesticide handbook (“The Pesticide Manual” 14thEd., British Crop Protection Council 2006) or can be found on theInternet (e.g. http://www.alanwood.netlpesticides).

(1) Acetylcholinesterase (AChE) inhibitors, such as, for example,

carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; ororganophosphates, for example acephate, azamethiphos, azinphos (-methyl,-ethyl), cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos,chlorpyrifos (-methyl), coumaphos, cyanophos, demeton-S-methyl,diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos,disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion,fenthion, fosthiazate, heptenophos, isofenphos, isopropylO-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion (-methyl), phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimiphos (-methyl),profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion,quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel antagonists, such as, for example,

organochlorines, for example chlordane and endosulfan (alpha-); orfiproles (phenylpyrazoles), for example ethiprole, fipronil,pyrafluprole and pyriprole.

(3) Sodium channel modulators/voltage-dependent sodium channel blockers,such as, for example, pyrethroids, for example acrinathrin, allethrin(d-cis-trans, d-trans), bifenthrin, bioallethrin,bioallethrin-S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin(beta-), cyhalothrin (gamma-, lambda-), cypermethrin (alpha-, beta-,theta-, zeta-), cyphenothrin [(1R)-trans-isomers], deltamethrin,dimefluthrin, empenthrin [(EZ)-(1R)-isomers], esfenvalerate, etofenprox,fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate(tau-), halfenprox, imiprothrin, metofluthrin, permethrin, phenothrin[(1R)-trans-isomer], prallethrin, profluthrin, pyrethrins (pyrethrum),resmethrin, RU 15525, silafluofen, tefluthrin, tetramethrin[(1R)-isomers], tralomethrin, transfluthrin and ZXI 8901; or

DDT; or methoxychlor.

(4) Nicotinergic acetylcholine receptor agonists, such as, for example,

neonicotinoids, for example acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid, thiamethoxam; ornicotine.

(5) Allosteric acetylcholine receptor modulators (agonists), such as,for example,

spinosyns, for example spinetoram and spinosad.

(6) Chloride channel activators, such as, for example,

avermectins/milbemycins, for example abamectin, emamectin benzoate,lepimectin and milbemectin.

(7) Juvenile hormone analogues, for example hydroprene, kinoprene,methoprene; or fenoxycarb; pyriproxyfen.

(8) Active compounds with unknown or non-specific mechanisms of action,such as, for example,

fumigants, for example methyl bromide and other alkyl halides; orchloropicrin; sulphuryl fluoride; borax; tartar emetic.

(9) Selective antifeedants, for example pymetrozine; or flonicamid.

(10) Mite growth inhibitors, for example clofentezine, diflovidazin,hexythiazox, etoxazole.

(11) Microbial disruptors of the insect gut membrane, such as, forexample, Bacillus thuringiensis subspecies israelensis, Bacillussphaericus, Bacillus thuringiensis subspecies aizawai, Bacillusthuringiensis subspecies kurstaki, Bacillus thuringiensis subspeciestenebrionis, and BT plant proteins, for example Cry1Ab, Cry1Ac, Cry1Fa,C2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1 .

(12) Oxidative phosphorylation inhibitors, ATP disruptors, such as, forexample, diafenthiuron; or

organotin compounds, for example azocyclotin, cyhexatin, fenbutatinoxide; orpropargite; tetradifon.

(13) Oxidative phoshorylation decouplers acting by interrupting the Hproton gradient, such as, for example, chlorfenapyr and DNOC.

(14) Nicotinergic acetylcholine receptor antagonists, such as, forexample, bensultap, cartap (hydrochloride), thiocylam, and thiosultap(sodium).

(15) Chitin biosynthesis inhibitors, type 0, such as, for example,benzoylureas, for example bistrifluoron, chlorfluazuron, diflubenzuron,flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron, teflubenzuron and triflumuron.

(16) Chitin biosynthesis inhibitors, type 1, such as, for example,buprofezin.

(17) Moulting disruptors, such as, for example, cyromazine.

(18) Ecdysone agonists/disruptors, such as, for example,diacylhydrazines, for example chromafenozide, halofenozide,methoxyfenozide and tebufenozide.

(19) Octopaminergic agonists, such as, for example, amitraz.

(20) Complex-III electron transport inhibitors, such as, for example,hydramethylnone; acequinocyl; fluacrypyrim.

(21) Complex-I electron transport inhibitors, for example from the groupof the METI acaricides, for example fenazaquin, fenpyroximate,pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; or

rotenone (Derris).

(22) Voltage-dependent sodium channel blockers, for example indoxacarb;metaflumizone.

(23) Inhibitors of acetyl-CoA carboxylase, such as, for example,tetronic acid derivatives, for example spirodiclofen and spiromesifen;or tetramic acid derivatives, for example spirotetramat.

(24) Complex-IV electron transport inhibitors, such as, for example,phosphines, for example aluminium phosphide, calcium phosphide,phosphine, zinc phosphide; or cyanide.

(25) Complex-II electron transport inhibitors, such as, for example,cyenopyrafen.

(28) Ryanodine receptor effectors, such as, for example, diamides, forexample flubendiamide, chlorantraniliprole (Rynaxypyr), cyantraniliprole(Cyazypyr) and also3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from WO2005/077934) or methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate(known from WO2007/043677).

Further active compounds with unknown mechanism of action, such as, forexample, azadirachtin, amidoflumet, benzoximate, bifenazate,chinomethionat, cryolite, cyflumetofen, dicofol, fluensulfone(5-chloro-2-[(3,4,4-trifluorobut-3-en-1-yl)sulphonyl]-1,3-thiazole),flufenerim, pyridalyl and pyrifluquinazon; and also products based onBacillus firmus (1-1582, BioNeem, Votivo) and also the known activecompounds below

4-{[(6-bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(6-fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(2-chloro-1,3-thiazol-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one(known from WO 2007/115643),4-{[(5,6-dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115646),4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one(known from WO 2007/115643),4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (knownfrom EP-A-0 539 588),4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one (known fromEP-A-0 539 588),[(6-chloropyridin-3-yl)methyl](methyl)oxido-λ⁴-sulphanylidenecyanamide(known from WO 2007/149134),[1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ⁴-sulphanylidenecyanamide(known from WO 2007/149134) and its diastereomers (A) and (B)

(also known from WO 2007/149134),[(6-trifluoromethylpyridin-3-yl)methyl](methyl)oxido-λ⁴-sulphanylidenecyanamide(known from WO 2007/095229), sulfoxaflor(also known from WO 2007/149134),11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one(known from WO 2006/089633),3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one(known from WO 2008/067911),1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO 2006/043635),[(3S,4aR,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-6,12-dihydroxy-4,12b-dimethyl-1′-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromen-4-yl]methylcyclopropanecarboxylate (known from WO 2006/129714),2-cyano-3-(difluoromethoxy)-N,N-dimethylbenzenesulphonamide (known fromWO2006/056433),2-cyano-3-(difluoromethoxy)-N-methylbenzenesulphonamide (known fromWO2006/100288), 2-cyano-3-(difluoromethoxy)-N-ethylbenzenesulphonamide(known from WO2005/035486),4-(difluoromethoxy)-N-ethyl-N-methyl-1,2-benzothiazole-3-amine1,1-dioxide (known from WO2007/057407) andN-[1-(2,3-dimethylphenyl)-2-(3,5-dimethylphenyl)ethyl]-4,5-dihydro-1,3-thiazole-2-amine(known from WO2008/104503).

Fungicides

(1) Ergosterol biosynthesis inhibitors, such as, for example, aldimorph,azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole,difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorphacetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole,fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol,flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole,imazalil, imazalil sulphate, imibenconazole, ipconazole, metconazole,myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol,pefurazoate, penconazole, piperalin, prochloraz, propiconazole,prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole,spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon,triadimenol, tridemorph, triflumizole, triforine, triticonazole,uniconazole, uniconazole-p, viniconazole, voriconazole,1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamideandO-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazole-1-carbothioate.

(2) Respiration inhibitors (respiratory-chain inhibitors), such as, forexample, bixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram,flutolanil, fluxapyroxad, furametpyr, furmecyclox, isopyrazam mixture ofthe syn-epimeric racemate 1RS,4SR,9RS and of the anti-epimeric racemate1RS,4SR,9SR, isopyrazam (anti-epimeric racemate), isopyrazam(anti-epimeric enantiomer 1R,4S,9S), isopyrazam (anti-epimericenantiomer 1S,4R,9R), isopyrazam (syn-epimeric racemate 1RS,4SR,9RS),isopyrazam (syn-epimeric enantiomer 1R,4S,9R), isopyrazam (syn-epimericenantiomer 1S,4R,9S), mepronil, oxycarboxin, penflufen, penthiopyrad,sedaxane, thifluzamid,1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamideandN-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.

(3) Respiration inhibitors (respiratory-chain inhibitors) on the complexIII of the respiratory chain, such as, for example, ametoctradin,amisulbrom, azoxystrobin, cyazofamid, dimoxystrobin, enestroburin,famoxadon, fenamidon, fluoxastrobin, kresoxim-methyl, metominostrobin,orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin,pyraoxystrobin, pyribencarb, trifloxystrobin,(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide,(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]-ethylidene}amino)oxy]methyl}phenyl)ethanamide,(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide,(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulphanyl)methyl]phenyl}-3-methoxyprop-2-enoate,N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamideand(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide.

(4) Mitosis and cell division inhibitors, such as, for example, benomyl,carbendazim, chlorfenazole, diethofencarb, ethaboxam, fluopicolid,fuberidazole, pencycuron, thiabendazole, thiophanate-methyl,thiophanate, zoxamide,5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidineand3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.

(5) Compounds with multi-site activity, such as, for example, Bordeauxmixture, captafol, captan, chlorothalonil, copper preparations such ascopper hydroxide, copper naphthenate, copper oxide, copper oxychloride,copper sulphate, dichlofluanid, dithianon, dodine, dodine free base,ferbam, fluorofolpet, folpet, guazatine, guazatine acetate,iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram-zinc, oxine-copper,propamidine, propineb, sulphur and sulphur preparations such as, forexample, calcium polysulphide, thiram, tolylfluanid, zineb and ziram.

(6) Resistance inductors, such as, for example, acibenzolar-S-methyl,isotianil, probenazole and tiadinil.

(7) Amino acid and protein biosynthesis inhibitors, such as, forexample, andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycinhydrochloride hydrate, mepanipyrim and pyrimethanil.

(8) ATP production inhibitors, such as, for example, fentin acetate,fentin chloride, fentin hydroxide and silthiofan.

(9) Cell wall synthesis inhibitors, such as, for example,benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamid,polyoxins, polyoxorim, validamycin A and valifenalate.

(10) Lipid and membrane synthesis inhibitors, such as, for example,biphenyl, chloroneb, dicloran, edifenphos, etridiazole, iodocarb,iprobenfos, isoprothiolane, propamocarb, propamocarb hydrochloride,prothiocarb, pyrazophos, quintozene, tecnazene and tolclofos-methyl.

(11) Melanin biosynthesis inhibitors, such as, for example, carpropamid,diclocymet, fenoxanil, fthalide, pyroquilon and tricyclazole.

(12) Nucleic acid synthesis inhibitors, such as, for example, benalaxyl,benalaxyl M (kiralaxyl), bupirimate, clozylacon, dimethirimol,ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M (mefenoxam),ofurace, oxadixyl and oxolinic acid.

(13) Signal transduction inhibitors, such as, for example, chlozolinate,fenpiclonil, fludioxonil, iprodione, procymidon, quinoxyfen andvinclozoline.

(14) Decouplers, such as, for example, binapacryl, dinocap, ferimzone,fluazinam and meptyldinocap.

(15) Further compounds, such as, for example, benthiazole, bethoxazin,capsimycin, carvone, chinomethionat, chlazafenon, cufraneb,cyflufenamid, cymoxanil, cyprosulfamide, dazomet, debacarb,dichlorophen, diclomezine, difenzoquat, difenzoquat methylsulphate,diphenylamine, ecomat, fenpyrazamine, flumetover, fluoromid,flusulfamide, flutianil, fosetyl-aluminium, fosetyl-calcium,fosetyl-sodium, hexachlorobenzene, irumamycin, methasulphocarb, methylisothiocyanate, metrafenone, mildiomycin, natamycin, nickeldimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb,oxyfenthiin, pentachlorophenol and its salts, phenothrin, phosphoricacid and its salts, propamocarb-fosetylate, propanosine-sodium,proquinazid, pyrroInitrin, tebufloquin, tecloftalam, tolnifanid,triazoxide, trichlamide, zarilamide,1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,1-(4-m ethoxyphenoxy)-3,3-d m ethylbutan-2-yl1H-imidazole-1-carboxylate,2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine,2,3-dibutyl-6-chlorothieno[2,3-d]pyrimdin-4(3H)-one,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{-4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,2-butoxy-6-iodo-3-propyl-4H-chromen-4-one,2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,2-phenylphenol and its salts,3,4,5-trichloropyridine-2,6-dicarbonitrile,3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine,3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,5-amino-1,3,4-thiadiazole-2-thiol,5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, ethyl(2Z)-3-amino-2-cyano-3-phenylprop-2-enoate,N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide,N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate,phenazine-1-carboxylic acid, quinolin-8-ol and quinolin-8-ol sulphate(2:1).

(16) Further compounds, such as, for example,1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-N-(4′-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide,N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,2-chloro-N-(4′-ethynylbiphenyl-2-yl)pyridine-3-carboxamide,2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide,5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanoneandN-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulphonyl)valinamide.

All of the stated co-components of classes (1) to (16) can form salts,where appropriate with suitable bases or acids, provided they arecapable of so doing on the basis of their functional groups.

A mixture with other known active compounds, such as herbicides,fertilizers, growth regulators, safeners, semiochemicals, or else withagents for improving the plant properties, is also possible.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergists. Synergists are compounds which increase theaction of the active compounds, without it being necessary for thesynergistic agent added to be active itself.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asmixtures with inhibitors which reduce degradation of the active compoundafter use in the environment of the plant, on the surface of parts ofplants or in plant tissues.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.00000001 to95% by weight of active compound, preferably between 0.00001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and geneticengineering methods or by combinations of these methods, including thetransgenic plants and including the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offshoots and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on the surroundings, habitat or storage space by thecustomary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(Genetically Modified Organisms), and parts thereof are treated. Theterms “parts”, “parts of plants” and “plant parts” have been explainedabove.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnovel properties (“traits”) which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. These can becultivars, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, higher quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possible,which exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (obtained by geneticengineering) which are preferably to be treated according to theinvention include all plants which, by virtue of the geneticmodification, received genetic material which imparts particularlyadvantageous, useful traits to these plants. Examples of such traits arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to water or soil salt content,increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, higher quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such traits are a better defense ofthe plants against animal and microbial pests, such as against insects,mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, sugar beet, tomatoes, peas and other vegetable varieties,cotton, tobacco, oilseed rape and also fruit plants (with the fruitsapples, pears, citrus fruits and grapes), and particular emphasis isgiven to maize, soya beans, potatoes, cotton, tobacco and oilseed rape.Traits that are emphasized in particular are increased defense of theplants against insects, arachnids, nematodes and slugs and snails byvirtue of toxins formed in the plants, in particular those formed in theplants by the genetic material from Bacillus thuringiensis (for exampleby the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2,Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (referredto hereinbelow as “Bt plants”). Traits that are also particularlyemphasized are the increased defense of the plants against fungi,bacteria and viruses by systemic acquired resistance (SAR), systemin,phytoalexins, elicitors and resistance genes and correspondinglyexpressed proteins and toxins. Traits that are furthermore particularlyemphasized are the increased tolerance of the plants to certainherbicidally active compounds, for example imidazolinones,sulphonylureas, glyphosate or phosphinotricin (for example the “PAT”gene). The genes which impart the desired traits in question can also bepresent in combination with one another in the transgenic plants.Examples of “Bt plants” which may be mentioned are maize varieties,cotton varieties, soya bean varieties and potato varieties which aresold under the trade names YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), StarLink® (for example maize),Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples ofherbicide-tolerant plants which may be mentioned are maize varieties,cotton varieties and soya bean varieties which are sold under the tradenames Roundup Ready® (tolerance to glyphosate, for example maize,cotton, soya beans), Liberty Link® (tolerance to phosphinotricin, forexample oilseed rape), IMI® (tolerance to imidazolinones) and STS®(tolerance to sulphonylureas, for example maize). Herbicide-resistantplants (plants bred in a conventional manner for herbicide tolerance)which may be mentioned include the varieties sold under the nameClearfield® (for example maize). Of course, these statements also applyto plant cultivars having these genetic traits or genetic traits stillto be developed, which plant cultivars will be developed and/or marketedin the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula I and/or the active compound mixtures according to theinvention. The preferred ranges stated above for the active compounds ormixtures also apply to the treatment of these plants. Particularemphasis is given to the treatment of plants with the compounds ormixtures specifically mentioned in the present text.

The active compounds according to the invention are active not onlyagainst plant pests, hygiene pests and stored-product pests but also inthe veterinary field against animal parasites (ecto and endoparasites)such as hard ticks, soft ticks, scab mites, harvest mites, flies(stinging and licking), parasitic fly larvae, lice, hair lice, bird liceand fleas. These parasites include:

from the order of the Anoplurida, for example Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.from the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.from the order of the Diptera and the suborders Nematocerina andBrachycerina, for example Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.from the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.from the order of the Heteropterida, for example Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp.from the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela gelmanica, Supella spp.from the subclass of the Acari (Acarina) and the orders of the Meta- andMesostigmata, for example Argas spp., Ornithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Varroa spp.from the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods, agricultural livestock suchas, for example, cattle, sheep, goats, horses, pigs, donkeys, camels,buffaloes, rabbits, chickens, turkeys, ducks, geese, honeybees, otherdomestic animals such as, for example, dogs, cats, cage birds, aquariumfish and what are known as experimental animals such as, for example,hamsters, guinea pigs, rats and mice. By controlling these arthropods itis intended to reduce deaths and improve performance (in the case ofmeat, milk, wool, hides, eggs, honey and the like) so that moreeconomical and simpler animal keeping is made possible by the use of theactive compounds according to the invention.

In the veterinary field and in animal keeping, the active compoundsaccording to the invention are applied in the known manner by enteraladministration in the form of, for example, tablets, capsules, drinks,drenches, granules, pastes, boluses, the feed-through method,suppositories, by parenteral administration, such as, for example, byinjections (intramuscular, subcutaneous, intravenous, intraperitonealand the like), implants, by nasal application, by dermal application inthe form of, for example, bathing or dipping, spraying, pouring-on andspotting-on, washing, dusting, and with the aid ofactive-compound-comprising shaped articles such as collars, ear tags,tail tags, limb bands, halters, marking devices and the like.

When used for livestock, poultry, domestic animals and the like, theactive compounds of the formula (I) can be applied as formulations (forexample powders, emulsions, flowables) which comprise the activecompounds in an amount of from 1 to 80% by weight, either directly orafter 100- to 10 000-fold dilution, or they can be used as a chemicalbath.

It has furthermore been found that the compounds according to theinvention also have a strong insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout any limitation:

Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobiumpertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendronspec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec. Dinoderus minutus;

Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur;

Termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitemiessantonensis, Reticulitermes lucifugus, Mastotemies darwiniensis,Zootermopsis nevadensis, Coptotennes formosanus;

Bristletails, such as Lepisma saccharina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cardboards, leather, wood and processed wood productsand coating compositions.

The ready-to-use compositions may, if appropriate, comprise furtherinsecticides and, if appropriate, one or more fungicides.

With respect to possible additional additives, reference may be made tothe insecticides and fungicides mentioned above.

The compounds according to the invention can likewise be employed forprotecting objects which come into contact with saltwater or brackishwater, in particular hulls, screens, nets, buildings, moorings andsignalling systems, against fouling.

Furthermore, the compounds according to the invention, alone or incombinations with other active compounds, may be employed as antifoulingagents.

In domestic, hygiene and stored-product protection, the active compoundsare also suitable for controlling animal pests, in particular insects,arachnids and mites, which are found in enclosed spaces such as, forexample, dwellings, factory halls, offices, vehicle cabins and the like.They can be employed alone or in combination with other active compoundsand auxiliaries in domestic insecticide products for controlling thesepests. They are active against sensitive and resistant species andagainst all developmental stages. These pests include:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleoptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix,Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of domestic insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricesters, carbamates, pyrethroids, neonicotinoids, growth regulators oractive compounds from other known classes of insecticides.

They are used in aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for scattering or in bait stations.

Elucidation of the Preparation Processes and Intermediates

The preparation examples and use examples which follow are illustrativebut not limitative of the invention.

PREPARATION EXAMPLE3-(Difluoromethyl)-1-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-1H-1,2,4-triazoleStage 1: 2,4-Dimethylhydrazine

Hydrochloric acid (89 g; 32% strength) and 40 ml of water are admixedwith 43 g of 2,4-dimethylaniline, and the suspension is cooled to −5 to−10° C. and then admixed dropwise with a solution of 25 g of sodiumnitrite and 104 ml of water, the aniline hydrochloride passing slowlyinto solution in the course of this addition. The clear, reddish brownsolution is made nitrite-free with a little amidosulphonic acid. Thisdiazonium salt solution, at a temperature of −10° C., is added rapidlydropwise to a solution of 200 g of SnCl₂.H₂O and 235 g of hydrochloricacid (32% strength). The resulting white suspension is stirred at thistemperature for a number of hours and the tin double salt is isolated bysuction filtration.

The tin double salt is added in a number of portions to an initialcharge of 100 g of sodium hydroxide solution (45% strength) and 100 g ofwater, the pH is adjusted to 14 and the hydrazine is separated off bymultiple MTBE extraction/ethyl acetate extraction from the aqueousphase. The solvent is distilled off under reduced pressure to give thehydrazine. Recrystallization from MTBE gives 45 g (93% of theory) of thepure 2,4-dimethylhydrazine.

M⁺: 136

¹H NMR (D6-DMSO): 6.85-6.97 (m, 3H), 3.7 (m, 3H), 2.25 (s, 3H), 2.1 (s,3H)

Stage 2: N′-(2,4-Dimethylphenyl)-2,2-difluoroacetohydrazide

An initial charge is prepared from 26.5 g of ethyl difluoroacetate and27 g of 2,4-dimethylphenylhydrazine in 100 ml of ethanol, and thismixture is stirred at 40° C. Following distillative removal of thesolvents, the residue is recrystallized, giving 27.24 g (67% of theory)(V).

logP: 1.8

M⁺: 214

¹H NMR (CDCl₃); 8.05 (s, 1H), 6.93-6.95 (m, 2H); 6.70-6.72 (d, 1H),5.90-6.17 (t, 1H), 2.25 (s, 3H), 2.24 (s, 3H)

Stage 3: 3-(Difluoromethyl)-1-(2,4-dimethylphenyl)-1H-1,2,4-triazole

An initial mixture of 50 g of triethyl orthoformate and 13.54 g ofammonium formate is admixed with 10 g ofN′-(2,4-dimethylphenyl)-2,2-difluoroacetohydrazide. After 24 hours, theorganic solvents are distilled off and the residue is stirred withdilute hydrochloric acid and methylene chloride. The methylene chloridephase is concentrated on a rotary evaporator and the crystalline residueis recrystallized from cyclohexane. Yield: 5.6 g (57% of theory).

logP(HCOOH): 2.43

M⁺: 223

¹H NMR (CDCl₃); 8.27 (s, 1H), 7.12-7.26 (m, 3H), 6.67-6.93 (t, 1H), 2.4(s, 3H), 2.19 (s, 3H)

Stage 4:5-[3-(Difluoromethyl)-1H-1,2,4-triazol-1-yl]-2,4-dimethylbenzenesulphonylchloride

Under a nitrogen atmosphere, 14.2 g of chlorosulphonic acid areintroduced and are admixed at room temperature, in portions, with 4 g of3-(difluoromethyl)-1-(2,4-dimethylphenyl)-1H-1,2,4-triazole. Theexothermic reaction raises the temperature of the mixture to around 45°C. The mixture is subsequently stirred at 70° C. for 5 hours and thencooled, and diluted with 20 ml of methylene chloride. The mixture isadded with stirring to 40 g of ice and then the phases are separated andextracted with twice 20 ml of methylene chloride. The combined organicphases are concentrated on a rotary evaporator. This gives 4.5 g ofbrown oil. This oil is chromatographed using CH₂Cl₂. A white solid (2.9g; 52% of theory) is isolated.

M⁺+1: 322

¹H NMR (CD₃CN): 8.61 (s, 1H), 8.11 (s, 1H), 7.61 (s, 1H), 6.92 (t, 1H),2.79 (s, 3H), 2.32 (s, 3H)

Stage 5:1,1′-[Disulphanediylbis(4,6-dimethylbenzene-3,1-diyl)]bis[3-(difluoromethyl)-1H-1,2,4-triazole]

A quantity of 5.4 g of5-[3-(difluoromethyl)-1H-1,2,4-triazol-1-yl]-2,4-dimethylbenzenesulphonylchloride is dissolved in 25 ml of glacial acetic acid, and 4.6 ml ofhydrochloric acid (32% strength) are added. The mixture is heated at120° C. (reflux). Then 2.53 g of iron powder in portions are added.Following complete reaction, the major part of glacial acetic acid isdistilled off, and water and dichloromethane are added. Following phaseseparation and concentration of the organic phase on a rotaryevaporator, and after chromatographic purification (CH₂Cl₂), 1.9 g(49.5% of theory) of a white solid are obtained.

M⁺: 508

¹H NMR (D6-DMSO): 9.00 (s, 2H), 7.62 (s, 2H), 7.40 (s, 2H), 7.09-7.27(t, 2H), 2.4 (s, 6H), 2.14 (s, 6H)

Stage 6:3-(Difluoromethyl)-1-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-1H-1,2,4-triazole(compound I-A-2)

Under nitrogen, 1 g of1,1′-[disulphanediylbis(4,6-dimethylbenzene-3,1-diyl)]bis[3-(difluoromethyl)-1H-1,2,4-triazole]is dissolved in 25 ml of DMF and the solution is admixed with 1.36 g ofsodium dithionite, 0.7 g of K₂CO₃ and 0.25 g of Rongalit and stirred at60° C. for 2 hours, after which 0.9 g of 2,2,2-trifluoroethane iodide isadded and the mixture is stirred until reaction is complete. The majoramount of the DMF is distilled off under reduced pressure and theresidue is stirred with water and methylene chloride. Followingconcentration of the organic phase on a rotary evaporator, the residueis chromatographed. This gives 0.75 g (57% of theory) of white solid.

logP (HCOOH): 3.33

M⁺: 337

¹H NMR (D6-DMSO): 9.04 (s, 1H), 7.68 (s, 1H), 7.38 (s, 1H), 7.17-7.30(t, 1H), 4.03-4.08 (m, 2H), 2.4 (s, 3H), 2.17 (s, 3H)

Stage 7:3-(Difluoromethyl)-1-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-1H-1,2,4-triazole(compound I-A-4)

A quantity of 0.5 g of3-(difluoromethyl)-1-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-1H-1,2,4-triazoleis added to 10 ml of dichloromethane and 0.33 g of meta-chloroperbenzoicacid in portions at 0-5° C. and the mixture is stirred at 0 to 5° C.until conversion is complete. Then 10 ml of water and 3 ml of NaHSO₃solution are added. The organic phase is separated off and washed withtwice 4 ml of saturated NaHCO₃ solution. Following phase separation, thesolvent is removed on a rotary evaporator and the residue ischromatographed with CH₂Cl₂/MTBE (19:1). This gives 0.25 g (47.7% oftheory) of (1-A-4).

logP(HCOOH): 2.19

M⁺: 353

¹H NMR (CD₃CN): 8.58 (s, 1H), 7.89 (s, 1H), 7.40 (s, 1H), 6.78-7.44 (m,1H), 3.55-3.75 (m, 2H), 2.42 (s, 3H), 2.26 (s, 3H).

The compounds of the formula (I) can be obtained in accordance with thepreparation process described above, examples being the followingcompounds of the formula (I):

logP logP Number Compound M⁺ + 1 (HCOOH) (H3PO4) NMR data I-A-1 

320 3.02 3.06 1H-NMR (D6-DMSO): 9.04 (s, 1H), 7.57 (s, 1H), 7.35 (s,1H), 7.03-7.12 (m, 1H), 6.13-6.32 (m, 1H), 3.52-3.58 (m, 2H), 2.37 (s,3H), 2.12 (s, 3H) I-A-2 

338 3.33 1H-NMR (D6-DMSO): 9.04 (s, 1H), 7.68 (s, 1H), 7.38 (s, 1H),7.17-7.30 (m, 1H), 4.03-4.08 (m, 2H), 2.40 (s, 3H), 2.17 (s, 3H) I-A-3 

336 1.9 1H-NMR (CD3CN); 8.58 (s, 1H), 7.86 (s, 1H), 7.39 (s, 1H),6.78-7.04 (t, 1H), 6.13-6.43 (m, 1H), 3.22- 3.50 (m, 2H), 2.4 (s, 3H),2.25 (s, 3H) I-A-4 

354 2.19 1H-NMR (CD3CN): 8.58 (s, 1H), 7.89 (s, 1H), 7.40 (s, 1H),6.78-7.44 (m, 1H), 3.55-3.75 (m, 2H), 2.42 (s, 3H), 2.26 (s, 3H) I-A-5 

3.24 1H-NMR (D6-DMSO): 9.45 (s, 1H), 7.99 (m, 1H), 7.67-7.69 (m, 1H),7.48 (d, 1H), 7.21 (t, 1H), 4.13 (q, 2H), 2.42 (s, 3H) I-A-6 

2.94 1H-NMR (D6-DMSO): 9.17 (s, 1H), 7.87 (d, 1H), 7.53 (d, 1H), 7.23(t, 1H), 6.08-6.38 (m, 1H), 3.50- 3.60 (m, 2H), 2.44 (s, 3H) I-A-7 

4.22 1H-NMR (D6-DMSO): 9.20-9.21 (m, 1H), 7.64 (s, 1H), 7.36 (s, 1H),6.08-6.38 (m, 1H), 3.50- 3.59 (m, 2H), 2.38 (s, 3H), 2.10 (s, 3H) I-A-8 

2.95 1H-NMR (D6-DMSO): 9.30-9.31 (m, 1H), 7.91 (s, 1H), 7.49 (s, 1H),6.31-6.60 (m, 1H), 3.48- 3.74 (m, 2H), 2.42 (s, 3H), 2.24 (s, 3H) I-A-9

3.28 1H-NMR (D6-DMSO): 9.50 (s, 1H), 8.09 (m, 1H), 7.77 (m, 2H), 7.23(t, 1H), 4.29 (q, 2H) I-A-10

3.27 1H-NMR (D6-DMSO): 9.31 (s, 1H), 7.96 (s, 1H), 7.51 (s, 1H),4.08-4.23 (m, 2H), 2.44 (s, 3H), 2.25 (s, 3H) I-A-11

3.11 1H-NMR (D6-DMSO): 9.29-9.30 (m, 1H), 7.83 (s, 1H), 7.44 (s, 1H),2.83-2.85 (m, 2H), 2.40 (s, 3H), 2.22 (s, 3H), 0.95-0.99 (m, 1H),0.54-0.57 (m, 2H), 0.26-0.30 (m, 2H) I-A-12

3.02 1H-NMR (D6-DMSO): 9.29 (s, 1H), 7.90 (s, 1H), 7.49 (s, 1H), 6.31-6.60 (m, 1H), 3.49- 3.72 (m, 2H), 2.42 (s, 3H), 2.23 (s, 3H) I-A-13

3.85 1H-NMR (D6-DMSO): 9.01 (s, 1H), 7.35 (s, 1H), 7.30 (s, 1H), 7.18(t, 1H), 2.93 (d, 2H), 2.33 (s, 3H), 2.09 (s, 3H), 0.98 - 1.04 (m, 1H),0.51- 0.56 (m, 2H), 0.23- 0.27 (m, 2H) I-A-14

5.11 1H-NMR (D6-DMSO): 9.18-9.19 (m, 1H), 7.43 (s, 1H), 7.31 (s, 1H),2.94 (d, 2H), 2.33 (s, 3H), 2.08 (s, 3H), 0.99-1.06 (m, 1H), 0.52-0.57(m, 2H), 0.24-0.28 (m, 2H) I-A-15

2.12 1H-NMR (D6-DMSO): 9.29-9.30 (m, 1H), 8.26 (d, 1H), 7.70 (d, 1H),7.28 (t, 1H), 4.15- 4.28 (m, 2H), 2.46 (s, 3H) I-A-16

2.1 1H-NMR (D6-DMSO): 9.55 (s, 1H), 8.31-8.32 (m, 1H), 8.03-8.05 (m,1H), 7.60 (d, 1H), 7.24 (t, 1H), 4.08-4.25 (m, 2H), 2.44 (s, 3H) I-A-17

2.28 1H-NMR (D6-DMSO): 9.12 (s, 1H), 7.75 (s, 1H), 7.47 (s, 1H), 7.20(t, 1H), 2.92-2.99 (m, 2H), 2.73- 2.84 (m, 2H), 2.41 (s, 3H), 2.25 (s,3H) I-A-18

3.01 1H-NMR (D6-DMSO): 9.03 (s, 1H), 7.28 (s, 1H), 7.25 (s, 1H), 7.19(t, 1H), 2.47 (s, 3H), 2.29 (s, 3H), 2.10 (s, 3H) I-A-19

3.37 1H-NMR (D6-DMSO): 9.01 (s, 1H), 7.62 (s, 1H), 7.36 (s, 1H), 7.19(t, 1H), 6.38-6.66 (m, 1H), 3.77 (t, 2H), 2.42 (s, 3H), 2.12 (s, 3H)I-A-20

2.47 1H-NMR (D6-DMSO): 9.02 (s, 1H), 7.61 (s, 1H), 7.42 (s, 1H), 7.20(t, 1H), 4.24 (s, 2H), 2.41 (s, 3H), 2.15 (s, 3H) I-A-21

1.46 1H-NMR (D6-DMSO): 9.12 (s, 1H), 7.79 (s, 1H), 7.44 (s, 1H), 7.20(t, 1H), 2.74 (s, 3H), 2.39 (s, 3H), 2.24 (s, 3H) I-A-22

1.37 1H-NMR (D6-DMSO): 9.23-9.24 (m, 1H), 8.16 (d, 1H), 7.62 (d, 1H),7.25 (t, 1H), 2.77 (s, 3H), 2.43 (s, 3H) I-A-23

1.81 1H-NMR (D6-DMSO): 9.26-9.27 (m, 1H), 8.20 (d, 1H), 7.66 (d, 1H),7.26 (t, 1H), 6.31-6.60 (m, 1H), 3.49-3.80 (m, 2H), 2.44 (s, 3H) I-A-24

2.31 1H-NMR (D6-DMSO): 9.17-9.18 (m, 1H), 7.94 (d, 1H), 7.62 (d, 1H),7.23 (t, 1H), 4.25 (s,2H), 2.47 (s, 3H) I-A-25

1.49 1H-NMR (D6-DMSO): 9.10 (s, 1H), 7.83 (s, 1H), 7.51 (s, 1H), 7.21(t, 1H), 4.66 (d, 1H), 4.37 (d, 1H), 2.43 (s, 3H), 2.27 (s, 3H) I-A-26

1.4 1H-NMR (D6-DMSO): 9.25-9.26 (m, 1H), 8.21 (d, 1H), 7.70 (d, 1H, 7.27(t, 1H), 4.72 (d, 1H), 4.41 (d, 1H), 2.46 (s, 3H) I-A-27

2.39 1H-NMR (D6-DMSO): 9.62 (s, 1H), 8.34-8.35 (m, 1H), 8.18-8.22 (m,1H), 7.92 (d, 1H), 7.26 (t, 1H), 4.16-4.37 (m, 2H) I-A-28

4.49 1H-NMR (D6-DMSO): 9.20 (s, 1H), 7.74 (s, 1H), 7.39 (s, 1H), 4.04(q, 2H), 2.41 (s, 3H), 2.11 (s, 3H) I-A-29

1.96 1H-NMR (D6-DMSO): 9.26-9.27 (m, 1H), 8.14 (d, 1H), 7.62 (d, 1H),7.27 (t, 1H), 2.82-2.91 (m, 2H), 2.42 (s, 3H), 0.97-1,00 (m, 1H),0.50-0.57 (m, 2H), 0.24-0.29 (m, 2H) I-A-30

3.28 1H-NMR (D6-DMSO): 9.17 (s, 1H), 7.98 (d, 1H), 7.56 (d, 1H), 7.23(t, 1H), 4.04 (q, 2H), 2.47 (s, 3H) I-A-31

3.81 1H-NMR (D6-DMSO): 9.15 (s, 1H), 7.66 (d, 1H), 7.48 (d, 1H), 7.22(t, 1H), 2.95 (d, 2H), 2.38 (s, 3H), 0.99-1.05 (m, 1H), 0.52-0.57 (m,2H), 0.25-0.28 (m, 2H) I-A-32

2.35 1H-NMR (D6-DMSO): 9.13 (s, 1H), 7.91 (s, 1H), 7.49 (s, 1H), 7.21(t, 1H), 6.39-6.68 (m, 1H), 3.69-3.91 (m, 2H), 2.42 (s, 3H), 2.27 (s,3H) I-A-33

2.05 1H-NMR (D6-DMSO): 9.11 (s, 1H), 7.77 (s, 1H), 7.42 (s, 1H), 7.20(t, 1H), 2.82-2.84 (m, 2H), 2.39 (s, 3H), 2.24 (s, 3H), 0.94-0.99 (m,1H), 0.53-0.56 (m, 2H), 0.25-0.29 (m, 2H) I-A-34

5.58 1H-NMR (D6-DMSO): 9.20 (s, 1H), 7.42 (s, 1H), 7.31 (s, 1H), 2.89(d, 2H), 2.33 (s, 3H), 2.07 (s, 3H), 1.81-1.87 (m, 1H), 1.00 (d, 6H)I-A-35

2.72 1H-NMR (D6-DMSO): 9.13 (s, 1H), 7.96 (s, 1H), 7.49 (s, 1H), 7.21(t, 1H), 4.08 (t, 2H), 2.43 (s, 3H), 2.27 (s, 3H) I-A-36

3.68 1H-NMR (D6-DMSO): 9.03 (s, 1H), 7.45 (s, 1H), 7.34 (s, 1H), 7.18(t, 1H), 3.17 (t, 2H), 2.54-2.67 (m, 2H), 2.34 (s, 3H), 2.12 (s, 3H)I-A-37

3.86 1H-NMR (D6-DMSO): 9.01 (s, 1H), 7.68 (s, 1H), 7.37 (s, 1H), 7.19(t, 1H), 4.02 (t, 2H), 2.43 (s, 3H), 2.13 (s, 3H) I-A-38

2.93 1H-NMR (D6-DMSO): 9.17 (s, 1H), 7.53 (d, 1H), 7.47 (d, 1H), 7.23(t, 1H), 2.52 (s, 3H), 2.33 (s, 3H) I-A-39

3.46 1H-NMR (D6-DMSO): 9.30 (s, 1H), 7.82 (s, 1H), 7.46 (s, 1H),2.65-2.77 (m, 2H), 2.12-2.19 (m ,1H), 1.02 (d, 3H), 1.13 (d, 3H)

The compounds of the formula (II-A) can be obtained in accordance withthe preparation processes described above, examples being the followingcompounds of the formula (II-A):

logP Number Compound (HCOOH) NMR data II-A-1

4.45 1H-NMR (D6-DMSO): 9.00 (s, 2H), 7.62 (s, 2H), 7.40 (s, 2H),7.09-7.27 (m, 2H), 2.4 (s, 6H), 2.14 (s, 6H) II-A-2

4.33 1H-NMR (D6-DMSO): 9.11 (s, 2H), 7.91 (d, 2H), 7.60 (d, 2H), 7.16(t, 2H), 2.46 (s, 6H) II-A-3

4.53 1H-NMR (D6-DMSO): 9.07 (s, 2H), 7.87 (s, 2H), 7.75 (s, 2H), 7.18(t, 2H), 2.45 (s, 6H) II-A-4

6.36 1H-NMR (D6-DMSO): 9.12 (s, 2H), 7.68 (s, 2H), 7.41 (s, 2H), 2.41(s, 6H), 2.12 (s, 6H) II-A-5

5.22 1H-NMR (D6-DMSO): 9.06 (s, 2H), 7.65 (s, 2H), 7.40 (s, 2H),6.79-7.07 (m, 2H), 2.40 (s, 6H), 2.12 (s, 6H) II-A-6

6.62 1H-NMR (D6-DMSO): 9.10 (s, 2H), 7.67 (s, 2H), 7.40 (s, 2H), 2.40(s, 6H), 2.12 (s, 6H) II-A-7

4.19 1H-NMR (D6-DMSO): 9.38 (s, 2H), 8.05-8.06 (m, 2H), 7.75-7.77 (m,2H), 7.50 (d, 2H), 7.15 (t, 2H), 2.47 (s, 6H)

The compounds of the formula (III-A) can be obtained in accordance withthe preparation processes described above, examples being the followingcompounds of the formula (III-A):

Number Compound NMR data III-A-1

1H-NMR (D6-DMSO): 9.16 (s, 1H), 8.07-8.10 (d, 1H), 7.37-7.40 (d, 1H),7.10-7.36 (t, 1H), 2.61 (s, 3H) III-A-2

1H-NMR (CD₃CN): 8.61 (s, 1H), 8.11 (s, 1H), 7.61 (s, 1H), 6.92 (t, 1H),2.79 (s, 3H), 2.32 (s, 3H) III-A-3

1H-NMR (D6-DMSO): 9.14 (s, 1H), 7.88 (s, 1H), 7.56 (s, 1H), 7.21 (t,1H), 2.61 (s, 3H) III-A-4

1H-NMR (D6-DMSO): 9.23 (s, 1H), 7.72 (s, 1H), 7.26 (s, 1H), 2.58 (s,3H), 2.17 (s, 3H) III-A-5

1H-NMR (D6-DMSO): 9.16 (s, 1H), 7.71 (s, 1H), 7.26 (s, 1H), 6.83-7.11(m, 1H), 2.58 (s, 3H), 2.13 (s, 3H) III-A-6

1H-NMR (D6-DMSO): 9.20-9.21 (m, 1H), 7.71 (s, 1H), 7.26 (s, 1H), 2.58(s, 3H), 2.12 (s, 3H) III-A-7

1H-NMR (D6-DMSO): 9.40 (s, 1H), 8.17- 8.18 (m, 1H), 7.70-7.73 (m, 1H),7.35 (d, 1H), 7.20 (t, 1H), 2.58 (s, 3H)

The compounds of the formula (IV-A) can be obtained in accordance withthe preparation processes described above, examples being the followingcompounds of the formula (IV-A):

logP Number Compound (HCOOH) NMR data IV-A-1

3.88 1H-NMR (D6-DMSO): 9.15-9.16 (m, 1H), 7.39-7.41 (m, 1H), 7.30 (s,1H), 7.21- 7.24 (m, 1H), 2.37 (s, 3H), 2.12 (s, 3H) IV-A-2

2.43 1H-NMR (CDCl₃); 8.27 (s, 1H), 7.12-7.26 (m, 3H), 6.67-6.93 (t, 1H),2.4 (s, 3H), 2.19 (s, 3H) IV-A-3

2.31 1H-NMR (D6-DMSO): 9.14 (s, 1H), 7.66- 7.70 (t, 1H), 7.39-7.42 (d,1H), 7.24- 7.26 (d, 1H), 7.08-7.35 (t, 1H), 2.41 (s, 3H) IV-A-4

2.46 1H-NMR (D6-DMSO): 9.01 (s, 1H), 7.59- 7.61 (m, 2H), 7.37-7.40 (m,1H), 7.20 (t, 1H), 2.42 (s, 3H) IV-A-5

3.78 1H-NMR (D6-DMSO): 9.18 (s, 1H), 7.41 (d, 1H), 7.30 (s, 1H), 7.23(d, 1H), 2.37 (s, 3H), 2.12 (s, 3H) IV-A-6

3.08 1H-NMR (D6-DMSO): 9.11 (s, 1H), 7.38 (d, 1H), 7.28-7.29 (m, 1H),7.20-7.23 (m, 1H), 6.82-7.13 (m, 1H), 2.37 (s, 3H), 2.12 (s, 3H) IV-A-7

2.26 1H-NMR (D6-DMSO): 9.39 (s, 1H), 7.74- 7.77 (m, 2H), 7.39-7.71 (m,2H), 7.19 (t, 1H), 2.42 (s, 3H)

The compounds of the formula (V) can be obtained in accordance with thepreparation processes described above, examples being the followingcompounds of the formula (V):

logP Number Compound (HCOOH) NMR data V-1

2.96 1H-NMR (D6-DMSO): 11.28 (s, 1H), 7.39 (s, 1H), 6.87 (s, 1H), 6.86(d, 1H), 6.48 (d, 1H), 2.17 (s, 3H), 2.14 (s, 3H) V-2

2.91 1H-NMR (D6-DMSO): 11.37 (s, 1H), 7.42 (s, 1H), 6.85-6.87 (m, 2H),6.46 (d, 1H), 2.17 (s, 3H), 2.14 (s, 3H) V-3

2.46 1H-NMR (D6-DMSO): 11.07 (s, 1H), 7.32 (s, 1H), 6.64-6.93 (m, 3H),6.47 (d, 1H), 2.16 (s, 3H), 2.14 (s, 3H) V-4

1.46 1H-NMR (D6-DMSO): 10.58-10.59 (m, 1H), 7.78-7.79 (m, 1H), 6.98 (d,2H), 6.64 (m, 2H), 6.35 (t, 1H), 2.18 (s, 3H) V-5

1.66 1H-NMR (D6-DMSO): 10.64 (s, 1H), 7.73 (s, 1H), 6.91-6.94 (d, 1H),6.82-6.84 (d, 1H), 6.65- 6.69 (t, 1H), 6.23-6.50 (t, 1H), 2.20 (s, 3H)

The compounds of the formula (X) can be obtained in accordance with thepreparation processes described above, examples being the followingcompounds of the formula (X):

logP Number Compound (HCOOH) NMR data X-1

2.5 X-2

3.65 1H-NMR (D6-DMSO): 7.38 (s, 1H), 7.07 (d, 1H), 6.87 (d, 1H), 6.84(s, 1H), 6.59 (s,2H), 2.17 (s, 3H), 2.16 (s, 3H) X-3

1.34

Analytical Methods

The logP values reported in the table above and in the preparationexamples were determined in accordance with EEC Directive 79/831 AnnexV.A8 by HPLC (High Performance Liquid Chromatography) on reversed-phasecolumns (C18), with the following methods:

^([a]) The determination is made in the acid range at pH 2.3 with 0.1%aqueous phosphoric acid and acetonitrile as eluents; linear gradientfrom 10% acetonitrile to 95% acetonitrile.

^([b]) The determination is made by LC-MS in the acid range at pH 2.7with 0.1% aqueous formic acid and acetonitrile (containing 0.1% formicacid) as eluents; linear gradient from 10% acetonitrile to 95%acetonitrile.

Calibration took place with unbranched alkan-2-ones (having 3 to 16carbon atoms) of known logP values (logP values determined from theretention times by linear interpolation between two successivealkanones).

The lambda-maX values were determined on the basis of the UV spectrafrom 200 nm to 400 nm in the maxima of the chromatographic signals.

The MH⁺ signals were determined using an Agilent MSD system with ESI andpositive or negative ionization.

The NMR spectra were determined using a Bruker Avance 400, equipped witha flow sample head (60 μl volume). Solvents used were d₆-DMSO or CD₃CN,with tetramethylsilane (0.00 ppm) used as a reference. The measurementtemperature is 303K when using d₆-DMSO as solvent, and 298K when usingCD₃CN as solvent.

In isolated cases, the samples were determined using a Bruker Avance II600 or III 600.

The splitting of the signals was described as follows: s (singlet), d(doublet), t (triplet), q (quartet), quin (quintet), m (multiplet).

USE EXAMPLES Example 1 Boophilus microplus Test (BOOPMI Injection)

Solvent: Dimethyl sulphoxide

An appropriate preparation of active compound is prepared by mixing 10mg of active compound with 0.5 ml of solvent and diluting theconcentrate with solvent to the desired concentration. The solution ofactive compound is injected into the abdomen (Boophilus microplus) andthe animals are transferred into dishes and kept in a controlledatmosphere. The activity is assessed on the basis of deposition offertile eggs.

After 7 days, the effect in % is determined. Here, 100% means that noneof the ticks has laid fertile eggs.

In this test the following compounds from the preparation examples, forexample, exhibit an activity of 100% for an application rate of 20μg/animal: I-A-1, I-A-2, I-A-3, I-A-4, I-A-5, I-A-7, I-A-8, I-A-9,I-A-10, I-A-11, I-A-12, I-A-17, I-A-27, I-A-36, I-A-39

Example 2 Phaedon Test (PHAECO Spray Treatment)

Solvents: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

An appropriate preparation of active compound is prepared by mixing 1part by weight of active compound with the stated amounts of solvent andemulsifier and diluting the concentrate with emulsifier-containing waterto the desired concentration. Leaf discs of Chinese cabbage (Brassicapekinensis) are sprayed with a preparation of active compound at thedesired concentration and, after they have dried, are populated withlarvae of the mustard beetle (Phaedon cochleariae).

After 7 days, the effect in % is determined. Here, 100% means that allof the beetle larvae have been killed; 0% means that no beetle larvaehave been killed.

In this test the following compounds from the preparation examples, forexample, show an effect of 100% for an application rate of 500 g/ha:I-A-5, I-A-6, I-A-9, I-A-10, I-A-12, I-A-15, I-A-16, I-A-23, I-A-27,I-A-30, I-A-31

Example 3 Tetranychus Test; OP Resistant (TETRUR Spray Treatment)

Solvents: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

An appropriate preparation of active compound is prepared by mixing 1part by weight of active compound with the stated amounts of solvent andemulsifier and diluting the concentrate with emulsifier-containing waterto the desired concentration. Leaf discs of bean (Phaseolus vulgaris)infested by all stages of the greenhouse red spidermite (Tetranychusurticae) are sprayed with a preparation of active compound at thedesired concentration.

After 6 days, the effect in % is determined. Here, 100% means that allof the mites have been killed; 0% means that no mites have been killed.

In this test the following compounds from the preparation examples, forexample, exhibit an effect of 80% for an application rate of 500 g/ha:I-A-21, I-A-22, IV-A-2

In this test the following compounds from the preparation examples, forexample, exhibit an effect of 90% for an application rate of 500 g/ha:IV-A-3, V-1

In this test the following compounds from the preparation examples, forexample, exhibit an effect of 100% for an application rate of 500 g/ha:I-A-2, I-A-10, I-A-15, I-A-18, I-A-20, I-A-23, I-A-24, I-A-25, I-A-26,I-A-29, I-A-33, I-A-38

In this test the following compounds from the preparation examples, forexample, exhibit an effect of 100% for an application rate of 100 g/ha:I-A-1, I-A-3, I-A-4, I-A-5, I-A-6, I-A-7, I-A-8, I-A-9, I-A-11, I-A-12,I-A-13, I-A-14, I-A-16, I-A-17, I-A-19, I-A-27, I-A-28, I-A-30, I-A-31,I-A-32, I-A-34, I-A-35, I-A-36, I-A-37, I-A-39

Example 4 Meloidogyne incognita Test (MELGIN)

Solvents: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

An appropriate preparation of active compound is prepared by mixing 1part by weight of active compound with the stated amounts of solvent andemulsifier and diluting the concentrate with water to the desiredconcentration. Pots are filled with sand, solution of active compound,meloidogyne incognita egg/larvae suspension, and lettuce seeds. Thelettuce seeds germinate and the plants develop. On the roots, the gallsdevelop. After 14 days, the nematicidal effect is determined from thegall formation, in %. Here, 100% means that no galls were found; 0%means that the number of galls on the treated plants corresponds to thatfor the untreated control.

In this test the following compounds from the preparation examples, forexample, show an effect of 90% for an application rate of 20 ppm:I-A-15, I-A-30

In this test the following compounds from the preparation examples, forexample, show an effect of 100% for an application rate of 20 ppm:I-A-2, I-A-4, I-A-9, I-A-16, I-A-27

Example 5 Tetranychus Test; OP Resistant (TETRUR Spray Treatment)

Solvents: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

An appropriate preparation of active compound is prepared by mixing 1part by weight of active compound with the stated amounts of solvent andemulsifier and diluting the concentrate with emulsifier-containing waterto the desired concentration.

Leaf discs of bean (Phaseolus vulgaris) infested by all stages of thegreenhouse red spidermite (Tetranychus urticae) are sprayed with apreparation of active compound at the desired concentration.

After the desired time, the effect in % is determined. Here, 100% meansthat all of the mites have been killed; 0% means that no mites have beenkilled.

In this test the following compounds from the preparation examples, forexample, exhibit an activity superior to the prior art:

see table

% effect Substance Structure Object Concentration after applicationVI-297 known from WO 1999/055668

TETRUR 20 g/ha  70 6d I-A-2 in accordance with the invention

TETRUR 20 g/ha 100 6d

1. A 3-[1-(3-Haloalkyl)triazolyl]phenyl sulphide of formula (I)

in which A¹ is CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂, CF₂Cl, CFCl₂ or(C₂-C₆)haloalkyl, A² is hydrogen, B⁰ is hydrogen, amino, halogen, cyano,nitro, alkyl, haloalkyl, alkylthio, haloalkylthio, alkoxy or haloalkoxy,B¹, B² and B³ independently of one another are each hydrogen, halogen,cyano, nitro, alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl,alkoxycarbonylalkyl, alkoxyalkyl, alkenyl, haloalkenyl, cyanoalkenyl,alkynyl, haloalkynyl, cyanoalkynyl, alkoxy, haloalkoxy, cyanoalkoxy,alkoxycarbonylalkoxy, alkoxyalkoxy, alkylthio, haloalkylthio,alkoxyalkylthio, alkylsulphinyl, halo alkyl sulphinyl,alkoxyalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,alkoxyalkylsulphonyl, acyl, haloalkylcarbonyl, carboxyl, alkoxycarbonylor NR³R⁴, where R³ and R⁴ independently of one another are hydrogen,alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl,alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl,acyl or alkoxycarbonyl, or R³ and R⁴, together with the N atom to whichthey are attached, may form an optionally substituted saturated orunsaturated, five- to eight-membered ring which is optionallyinterrupted by heteroatoms, n is the number 0, 1 or 2, R¹ is hydrogen oralkyl, and R² is hydrogen, halogen, cyano, nitro, alkyl, haloalkyl,cyanoalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl orhaloalkoxyalkyl, or is optionally substituted cycloalkyl or cycloalkenyleach of which is optionally interrupted by one or more heteroatoms. 2.The 3-[1-(3-Haloalkyl)triazolyl]phenyl sulphide according to claim 1, inwhich A¹ is CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂ CF₂Cl, CFCl₂ or(C₂-C₆)haloalkyl, A² is hydrogen, B⁰ is hydrogen, amino, halogen, cyano,nitro, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy or (C₁-C₆)haloalkoxy, B¹, B² and B³independently of one another are each hydrogen, halogen, cyano, nitro,(C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,(C₂-C₇)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₂-C₅)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₃)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylthio, (C₁-C₆)halo alkylthio, (C₁-C₃)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylsulphinyl, (C₁-C₆)haloalkylsulphinyl,(C₁-C₃)alkoxy-(C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)haloalkylsulphonyl, (C₁-C₃)alkoxy-(C₁-C₆)alkylsulphonyl,(C₁-C₇)acyl, (C₂-C₅)haloalkylcarbonyl, carboxyl, (C₂-C₇)alkoxycarbonylor NR³R⁴, where R³ and R⁴ independently of one another are hydrogen,(C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₇)acyl,(C₂-C₇)alkoxycarbonyl, or R³ and R⁴, together with the N atom to whichthey are attached, may form an optionally (C₁-C₄)alkyl-, (C₁-C₄)alkoxy-,(C₁-C₄)haloalkyl-substituted saturated or unsaturated, five- orsix-membered ring which is optionally interrupted by heteroatoms, n isthe number 0, 1 or 2, R¹ is hydrogen or (C₁-C₄)alkyl, and R² ishydrogen, halogen, cyano, nitro, (C_(I)-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl or(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, or is optionally substituted(C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkenyl each of which is optionallyinterrupted by one or more heteroatoms.
 3. A process for preparing the3-[1-(3-Haloalkyl)triazolyl]phenyl sulphide according to claim 1comprising (A) (i) reacting an aniline of formula (VII)

with sodium nitrite to give a diazonium salt, (ii) reducing thediazonium salt to give a hydrazine of formula (VI)

(B) reacting the hydrazine of formula (VI) with an ester of formula(VIII)

where A^(1a) is alkyl, to give a hydrazide of formula (V)

(C) reacting the hydrazide of formula (V) with formamidine hydrochloridein the presence of a base to give a triazole of formula (IV-A)

(D) sulphochlorinating the triazole of formula (IV-A) to give asulphonyl chloride of formula (III-A)

(E) reducing the sulphonyl chloride of formula (III-A) to provide adisulphide of formula (II-A)

(F) reacting the disulphide of formula (II-A) with an electrophile offormula (IX)

where AG is a leaving group, to give a sulphide of formula (I-Aa)

(G) reacting the sulphide of formula (I-Aa) with an oxidizing agent togive a sulphoxide of formula (I-Ab)

and sulphones of formula (I-Ac)


4. The process according to claim 3, wherein the triazole of formula(IV-A) is prepared by reacting a boronic acid of formula (VIII)

with a triazole of formula (IX-A)

and with a copper catalyst.
 5. The process according to claim 3, whereinthe triazole of formula (IV-A) is prepared by reacting a hydrazine offormula (VI)

with an amidine of formula (XI) or a salt thereof

to give an amidrazone of formula (X)

reacting the amidrazone with an orthoformate.
 6. An active compoundcomposition comprising at least one 3-[1-(3-haloalkyl)triazolyl]phenylsulphide of formula (I) according to claim 1 and at least one otheractive insecticidal, acaricidal or nematicidal compound selected fromthe group consisting of (1) Acetylcholinesterase (AChE) inhibitors; (2)GABA-gated chloride channel antagonists; (3) Sodium channel modulators;(4) Nicotinergic acetylcholine receptor agonists; (5) Allostericacetylcholine receptor modulators; (6) Chloride channel activators; (7)Juvenile hormone analogues; (8) Active compounds with unknown ornon-specific mechanisms of action; (9) Selective antifeedants; (10) Mitegrowth inhibitors; (11) Microbial disruptors of the insect gut membrane;(12) Oxidative phosphorylation inhibitors; (13) Oxidative phoshorylationdecouplers acting by interrupting a H proton gradient; (14) Nicotinergicacetylcholine receptor antagonists; (15) Chitin biosynthesis inhibitors,type 0; (16) Chitin biosynthesis inhibitors, type 1; (17) Moultingdisruptors; (18) Ecdysone agonists/disruptors; (19) Octopaminergicagonists; (20) Complex-III electron transport inhibitors; (21) Complex-Ielectron transport inhibitors; (22) Voltage-dependent sodium channelblockers; (23) Inhibitors of acetyl-CoA carboxylase; (24) Complex-IVelectron transport inhibitors; (25) Complex-II electron transportinhibitors; (26) Ryanodine receptor effectors; (27) Further activecompounds with unknown mechanism of action selected from the groupconsisting of azadirachtin, amidoflumet, benzoximate, bifenazate,chinomethionat, cryolite, cyflumetofen, dicofol, fluensulfone(5-chloro-2-[(3,4,4-trifluorobut-3-en-1-yl)sulphonyl]-1,3-thiazole),flufenerim, pyridalyl, pyrifluquinazon, products based on Bacillusfirmuus,4-{[(6-bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one,4-{[(6-fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one,4-{[(2-chloro-1,3-thiazol-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one,4-{[(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one,4-{[(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one,4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one,4-{[(5,6-dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one,4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one,4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one,4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one,[(6-chloropyridin-3-yl)methyl](methyl)oxido-λ⁴-sulphanylidenecyanamide,[1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ⁴-sulphanylidenecyanamideand its diastereomers (A) and (B)

[(6-trifluoromethylpyridin-3-yl)methyl](methyl)oxido-λ⁴-sulphanylidenecyanamide,sulfoxaflor,11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one,3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine,[(3S,4aR,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-6,12-dihydroxy-4,12b-dimethyl-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromen-4-yl]methylcyclopropanecarboxylate,2-cyano-3-(difluoromethoxy)-N,N-dimethylbenzenesulphonamide,2-cyano-3-(difluoromethoxy)-N-methylbenzenesulphonamide,2-cyano-3-(difluoromethoxy)-N-ethylbenzenesulphonamide,4-(difluoromethoxy)-N-ethyl-N-methyl-1,2-benzothiazole-3-amine1,1-dioxide andN-[1-(2,3-dimethylphenyl)-2-(3,5-dimethylphenyl)ethyl]-4,5-dihydro-1,3-thiazole-2-amine,and/or at least one further active fungicidal compound selected from thegroup consisting of (28) Ergosterol biosynthesis inhibitors; (29)Respiration inhibitors; (30) Respiration inhibitors on complex III of arespiratory chain; (31) Mitosis and cell division inhibitors; (32)Compounds with multi-site activity; (33) Resistance inductors; (34)Amino acid and protein biosynthesis inhibitors; (35) ATP productioninhibitors; (36) Cell wall synthesis inhibitors; (37) Lipid and membranesynthesis inhibitors; (38) Melanin biosynthesis inhibitors; (39) Nucleicacid synthesis inhibitors; (40) Signal transduction inhibitors; (41)Decouplers; (42) Further compounds selected from the group consisting ofbenthiazole, bethoxazin, capsimycin, carvone, chinomethionat,chlazafenon, cufraneb, cyflufenamid, cymoxanil, cyprosulfamide, dazomet,debacarb, dichlorophen, diclomezine, difenzoquat, difenzoquatmethylsulphate, diphenylamine, ecomat, fenpyrazamine, flumetover,fluoromid, flusulfamide, flutianil, fosetyl-aluminium, fosetyl-calcium,fosetyl-sodium, hexachlorobenzene, irumamycin, methasulphocarb, methylisothiocyanate, metrafenone, mildiomycin, natamycin, nickeldimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb,oxyfenthiin, pentachlorophenol and a salt thereof, phenothrin,phosphoric acid or a salt thereof, propamocarb-fosetylate,propanosine-sodium, proquinazid, pyrroInitrin, tebufloquin, tecloftalam,tolnifanid, triazoxide, trichlamide, zarilamide,1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl 1H-imidazole-1-carboxylate,2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine,2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{-4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,2-butoxy-6-iodo-3-propyl-4H-chromen-4-one,2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,2-phenylphenol and its salts,3,4,5-trichloropyridine-2,6-dicarbonitrile,3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine,3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,5-amino-1,3,4-thiadiazole-2-thiol,5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, ethyl(2Z)-3-amino-2-cyano-3-phenylprop-2-enoate,N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide,N-{(E)-[(cyclopropylmethoxy)imino][6-(di fluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N—[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methyliden]amino}oxy)methyl]pyridin-2-yl}carbamate,phenazin-1-carboxylic acid, quinoline-8-ol, quinoline-8-ol sulphate,1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-N-(4′-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide,N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,2-chloro-N-(4′-ethynylbiphenyl-2-yl)pyridine-3-carboxamide,2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide,5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone andN-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N-2-(methylsulphonyl)valinamide.7. A composition comprising at least one3-[1-(3-Haloalkyl)triazolyl]phenyl sulphide of formula (I) according toclaim 1 and at least one penetrant.
 8. A disulphide of formula (II-A)

wherein A¹ is CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂, CF₂Cl, CFCl₂ or(C₂-C₆)haloalkyl, B⁰ is hydrogen, amino, halogen, cyano, nitro, alkyl,haloalkyl, alkylthio, haloalkylthio, alkoxy or haloalkoxy, B² ishydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cyanoalkyl,hydroxyalkyl, alkoxycarbonylalkyl, alkoxyalkyl, alkenyl, haloalkenylcyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, alkoxy, haloalkoxy,cyanoalkoxy, alkoxycarbonylalkoxy, alkoxyalkoxy, alkylthio,haloalkylthio, alkoxyalkylthio, alkylsulphinyl, haloalkylsulphinyl,alkoxyalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,alkoxyalkylsulphonyl, acyl, haloalkylcarbonyl, carboxyl, alkoxycarbonylor NR³R⁴, where R³ and R⁴ independently of one another are hydrogen,alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl,alkenyl, haloalkenyl, cyanoalkynyl, alkynyl, haloalkynyl, cyanoalkynyl,acyl or alkoxycarbonyl, or R³ and R⁴, together with the N atom to whichthey are attached, may form an optionally substituted saturated orunsaturated, five- to eight-membered ring which is optionallyinterrupted by heteroatoms, and B¹ and B³ are hydrogen.
 9. A sulphonylchloride of formula (III-A)

wherein A¹ is CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂, CF₂Cl, CFCl₂ or(C₂-C₆)haloalkyl, B⁰ is hydrogen, amino, halogen, cyano, nitro, alkyl,haloalkyl, alkylthio, haloalkylthio, alkoxy or haloalkoxy, B² ishydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cyanoalkyl,hydroxyalkyl, alkoxycarbonylalkyl, alkoxyalkyl, alkenyl, haloalkenyl,cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, alkoxy, haloalkoxy,cyanoalkoxy, alkoxycarbonylalkoxy, alkoxyalkoxy, alkylthio,haloalkylthio, alkoxyalkylthio, alkylsulphinyl, haloalkylsulphinyl,alkoxyalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,alkoxyalkylsulphonyl, acyl, haloalkylcarbonyl, carboxyl, alkoxycarbonylor NR³R⁴, where R³ and R⁴ independently of one another are hydrogen,alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl,alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl,acyl or alkoxycarbonyl, or R³ and R⁴, together with the N atom to whichthey are attached, may form an optionally substituted saturated orunsaturated, five- to eight-membered ring which is optionallyinterrupted by heteroatoms, and B¹ and B³ are hydrogen.
 10. A triazoleof formula (IV-A)

where A¹ is CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂, CF₂Cl, CFCl₂ or(C₂-C₆)haloalkyl, B⁰ is hydrogen, amino, halogen, cyano, nitro, alkyl,haloalkyl, alkylthio, haloalkylthio, alkoxy or haloalkoxy, B² ishydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cyanoalkyl,hydroxyalkyl, alkoxycarbonylalkyl, alkoxyalkyl, alkenyl, haloalkenyl,cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, alkoxy, haloalkoxy,cyanoalkoxy, alkoxycarbonylalkoxy, alkoxyalkoxy, alkylthio,haloalkylthio, alkoxyalkylthio, alkylsulphinyl, haloalkylsulphinyl,alkoxyalkylsulphinyl, alkylsulphonyl, halo alkylsulphonyl,alkoxyalkylsulphonyl, acyl, haloalkylcarbonyl, carboxyl, alkoxycarbonylor NR³R⁴, where R³ and R⁴ independently of one another are hydrogen,alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl,alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl,acyl or alkoxycarbonyl, or R³ and R⁴, together with the N atom to whichthey are attached, may form an optionally substituted saturated orunsaturated, five- to eight-membered ring which is optionallyinterrupted by heteroatoms, and B¹ and B³ are hydrogen, and if A¹ isCHF₂, CF₂CHF₂ or CF₂CF₂Cl, B⁰ is hydrogen, methyl, ethyl, fluoro,chloro, methoxy, cyano, CHF₂, CF₃ or OCF₃, B² is hydrogen, methyl,ethyl, fluoro, chloro, methoxy, cyano, CHF₂, CF₃ or OCF₃, and if A¹ isCF₂CF₃, B⁰ is hydrogen, methyl, ethyl, fluoro, methoxy, cyano, CHF₂, CF₃or OCF₃, B² is methyl, ethyl, fluoro, chloro, methoxy, cyano, CHF₂, CF₃or OCF₃.
 11. A hydrazide of formula (V)

where B¹ and B³ are hydrogen, A¹ is CHF₂, CF₂CF₃, CF₂CHF₂ or CF₂CF₂Cl,B⁰ is methyl, ethyl, fluoro, chloro, methoxy, cyano, CHF₂, CF₃ or OCF₃,B² is hydrogen, methyl, methoxy, ethyl, fluoro, chloro, cyano, CHF₂, CF₃or OCF₃, and B² is not methyl if A¹ is CHF₂, and B² is not methoxy if A¹is CF₂CF₃.
 12. An amidrazone of formula (X)

where A¹ is CH₂F, CF₂CF₃, CF₂CHF₂ or CF₂CF₂Cl, B⁰ is hydrogen, methyl,ethyl, fluoro, chloro, methoxy, cyano, CHF₂, CF₃ or OCF₃, B¹ and B³independently of one another are each hydrogen, halogen, cyano, nitro,alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxycarbonylalkyl,alkoxyalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl,cyanoalkynyl, alkoxy, haloalkoxy, cyanoalkoxy, alkoxycarbonylalkoxy,alkoxyalkoxy, alkylthio, haloalkylthio, alkoxyalkylthio, alkylsulphinyl,haloalkylsulphinyl, alkoxyalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkoxyalkylsulphonyl, acyl, haloalkylcarbonyl, carboxyl,alkoxycarbonyl or NR³R⁴, where R³ and R⁴ independently of one anotherare hydrogen, alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl,alkylthioalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl,haloalkynyl, cyanoalkynyl, acyl or alkoxycarbonyl, or R³ and R⁴,together with the N atom to which they are attached, may form anoptionally substituted saturated or unsaturated, five- to eight-memberedring which is optionally interrupted by heteroatoms, and B² is hydrogen,methyl, ethyl, fluoro, chloro, methoxy, cyano, CHF₂, CF₃ or OCF₃, and B²is not hydrogen if A¹ is CF₂CF₃.
 13. An agrochemical compositioncomprising at least one 3-[1-(3-Haloalkyl)triazolyl]phenyl sulphide offormula (I) according to claim 1 and extenders and/or surface-activesubstances.
 14. A method of controlling animal pests, in the protectionof materials and/or in the veterinary sector comprising applying the3-[1-(3-Haloalkyl)triazolyl]phenyl sulphide of formula (I) according toclaim 1 to animal pests and/or to a habitat of the animal pests.